(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

Base Information

Chemical Name:(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol
CAS No.:95531-91-2
Molecular Formula:C₂₆H₃₈O₄
Molecular Weight:414.585
Hs Code.:

Synonyms:(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

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Chemical Property of (1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

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Technology Process of (1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

There total 12 articles about (1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 95532-02-8
(4R,4aR,8aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-4a-methyl-octahydro-naphthalen-2-one

: 95531-91-2
(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) sodium herxamethyldisilazide / tetrahydrofuran / 1.) 0 degC, 7 h; 2.) -78 degC, 1 h

2: 89 percent / potassium tert-butoxide, sodium iodide / hexamethylphosphoric acid triamide / 6 h / 60 °C

3: 86 percent / nonane / 36 h / Heating

4: 69 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / 0 °C

5: 1.) triethylamine, tert-butyldimethylsilyl trifluoromethanesulfonate; 2.) lithium aluminum hydride / 1.) ether, 25 degC, 2.5 h; 2.) 4 h, 25 degC

6: 99 percent / p-toluenesulfonic acid / 1.5 h / 25 °C

7: tetra-n-butylammonium fluoride / tetrahydrofuran / 7 h / Heating

8: pyridinium dichromate / CH₂Cl₂ / 4 h / 25 °C

9: 70 percent / stannic chloride / CH₂Cl₂ / 0.08 h / 0 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; t-butyldimethylsiyl triflate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; nonane; hexane; dichloromethane;
DOI:10.1021/ja00295a027

Reference yield:

: 95531-79-6
(1R,2R,4aS,8aR)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-8a-methyl-3-oxo-decahydro-naphthalene-2-carboxylic acid methyl ester

: 95531-91-2
(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / potassium tert-butoxide, sodium iodide / hexamethylphosphoric acid triamide / 6 h / 60 °C

2: 86 percent / nonane / 36 h / Heating

3: 69 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / 0 °C

4: 1.) triethylamine, tert-butyldimethylsilyl trifluoromethanesulfonate; 2.) lithium aluminum hydride / 1.) ether, 25 degC, 2.5 h; 2.) 4 h, 25 degC

5: 99 percent / p-toluenesulfonic acid / 1.5 h / 25 °C

6: tetra-n-butylammonium fluoride / tetrahydrofuran / 7 h / Heating

7: pyridinium dichromate / CH₂Cl₂ / 4 h / 25 °C

8: 70 percent / stannic chloride / CH₂Cl₂ / 0.08 h / 0 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; t-butyldimethylsiyl triflate; potassium tert-butylate; tetrabutyl ammonium fluoride; tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; nonane; hexane; dichloromethane;
DOI:10.1021/ja00295a027

Reference yield:

: 95531-78-5
(4S,4aS,8aR)-4-Hydroxymethyl-4a-methyl-octahydro-naphthalen-2-one

: 95531-91-2
(1R,4R,4bR,8aS,10R,10aR)-1-(2-Benzyloxy-ethyl)-10a-hydroxymethyl-4b-methyl-2-methylene-tetradecahydro-phenanthrene-4,10-diol

Guidance literature:: Multi-step reaction with 10 steps

1: 91 percent / triethylamine, 4-dimethylaminopyridine / CH₂Cl₂ / 4 h / 25 °C

2: 1.) sodium herxamethyldisilazide / tetrahydrofuran / 1.) 0 degC, 7 h; 2.) -78 degC, 1 h

3: 89 percent / potassium tert-butoxide, sodium iodide / hexamethylphosphoric acid triamide / 6 h / 60 °C

4: 86 percent / nonane / 36 h / Heating

5: 69 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / 0 °C

6: 1.) triethylamine, tert-butyldimethylsilyl trifluoromethanesulfonate; 2.) lithium aluminum hydride / 1.) ether, 25 degC, 2.5 h; 2.) 4 h, 25 degC

7: 99 percent / p-toluenesulfonic acid / 1.5 h / 25 °C

8: tetra-n-butylammonium fluoride / tetrahydrofuran / 7 h / Heating

9: pyridinium dichromate / CH₂Cl₂ / 4 h / 25 °C

10: 70 percent / stannic chloride / CH₂Cl₂ / 0.08 h / 0 °C

With dmap; lithium aluminium tetrahydride; dipyridinium dichromate; t-butyldimethylsiyl triflate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tin(IV) chloride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; nonane; hexane; dichloromethane;
DOI:10.1021/ja00295a027